Highly regioselective rearrangement of 2-substituted vinylepoxides catalyzed by gallium(III) triflate

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6537-6540

  Deng, Xian Ming ^a   Sun, Xiu Li ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CARBONYLATION; CATALYSIS; KETONES; SUBSTITUTION REACTIONS; VINYL RESINS;

CARBONYL COMPOUNDS; CHEMOSELECTIVITY; REGIOSELECTIVITY; VINYLEPOXIDES;

GALLIUM COMPOUNDS;

CARBONYL DERIVATIVE; EPOXIDE; GALLIUM; GALLIUM TRIFLATE; TRIMETHYLSILYLVINYL EPOXIDE; UNCLASSIFIED DRUG; VINYL EPOXIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 23044492621     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050810z     Document Type: Article

References (48)

1. For reviews, see: (a) Parker, R. E.; Issacs, N. S. Chem. Rev. 1959, 59, 737.
2. (b) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323.
3. (c) Smith, J. G. Synthesis 1984, 629.
4. For a review, see: Silva, L. F., Jr. Tetrahedron 2002, 58, 9137.
5. Selected references: (a) Kita, Y.; Higuchi, K.; Yoshida, Y.; Iio, K.; Kitagaki, S.; Uede, K.; Akai, S.; Fujioka, H. J. Am. Chem. Soc. 2001, 123, 3214.
6. (b) Grellepois, F.; Chorki, F.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J. P. J. Org. Chem. 2002, 67, 1253.
7. (c) Kimura, T.; Yamamoto, N.; Suzuki, Y.; Kawano, K.; Norimine, Y.; Ito, K.; Nagato, S.; Iimura, Y.; Yonaga, M. J. Org. Chem. 2002, 67, 6228.
8. (d) Tinder, J. E.; Tanner, D. Tetrahedron 2003, 59, 6937.
9. For a review, see: Rickborn, B. Acid-catalyzed Rearrangements of Epoxides in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 3.3, pp 733-775.
10. See, for example, the following. Organoaluminum reagent: (a) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431.
11. (b) Maruoka, K.; Ooi, T.; Nagahara, S.; Yamamoto, H. Tetrahedron 1991, 47, 6983.
12. (c) Maruoka, K.; Ooi, T.; Yamamoto, H. Tetrahedron 1992, 48, 3303.
13. (d) Maruoka, K.; Murase, N.; Bureau, R.; Ooi, T.; Yamamoto, H. Tetrahedron 1994, 50, 3663.
14. 3: Ishihara, K.; Hanaki, N.; Yamamoto, H. Synlett 1995, 721.
15. (f) Pd(0) catalyst: Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195.
16. 4: Sudha, R.; Narasimhan, K. M.; Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1996, 61, 1877.
17. 3: Ranu, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212.
18. 2O: Anderson, A. M.; Blazek, J. M.; Garg, P.; Payne, B. J.; Mohan, R. S. Tetrahedron Lett. 2000, 41, 1527.
19. 2O: Bhatia, K. A.; Eash, K. J.; Leonard, N. M.; Oswald, M. C.; Mohan, R. S. Tetrahedron Lett. 2001, 42, 8129.
20. 2: Martinez, F.; Campo, C.; Llama, E. F. J. Chem. Soc., Perkin Trans. 1 2000, 1749.
21. 3: Procopio, A.; Dalpozzo, R.; Nino, A. D.; Nardi, M.; Sindona, G.; Tagarelli, A. Synlett 2004, 2633.
22. For metalloporphyrin-catalyzed rearrangement, see the following, (a) Fe(TPP)OTf: Takanami, T.; Hirabe, R.; Ueno, M.; Hino, F.; Suda, K. Chem. Lett. 1996, 1031.
23. 4: Suda, K.; Baba, K.; Nakajima, S.; Takanami, T. Tetrahedron Lett. 1999, 40, 7243.
24. (c) Suda, K.; Baba, K.; Nakajima, S.; Takanami, T. Chem. Commun. 2002, 2570.
25. (d) Cr(TPP)OTf: Suda, K.; Kikkawa, T.; Nakajima, S.; Takanami, T. J. Am. Chem. Soc. 2004, 126, 9554.
26. For recent acid-catalyzed rearrangement of enol ester epoxides, see: (a) Zhu, Y.; Manske, K. J.; Shi, Y. J. Am. Chem. Soc. 1999, 121, 4080.
27. (b) Feng, X.; Shu, L.; Shi, Y. J. Am. Chem. Soc. 1999, 121, 11002.
28. (c) Zhu, Y.; Shu, L.; Tu, Y.; Shi, Y. J. Org. Chem. 2001, 66, 1818.
29. (d) Feng, X.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2831.
30. Rosenberger, M.; Jackson, W.; Saucy, G. Helv. Chim. Acta 1980, 63, 175.
31. 3-promoted rearrangements of vinyl epoxides: (a) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379.
32. (b) Jung, M. E.; Anderson, K. L. Tetrahedron Lett. 1997, 35, 2605.
33. (c) Jung, M. E.; Marquez R. Tetrahedron Lett. 1999, 40, 3129.
34. For rearrangement catalyzed by Pd(0), see: (a) Gilloir, F.; Malacria, M. Tetrahedron Lett. 1992, 33, 3859.
35. (b) Bideau, F. L.; Aubert, C.; Malacria, M. Tetrahedron: Asymmetry 1995, 6, 697.
36. (c) Bideau, F. L.; Gilloir, F.; Nilson, Y.; Aubert, C.; Malacria, M. Tetrahedron 1996, 52, 7487.
37. (d) Courillon, C.; Fol, R. L.; Vandendris, E.; Malacria, M. Tetrahedron Lett. 1997, 35, 5493.
38. (a) Huang, Z.-Z.; Ye, S.; Xia, W.; Tang, Y. Chem. Commun. 2001, 1384.
39. (b) Ye, S.; Huang, Z.-Z.; Xia, C.-A.; Tang, Y.; Dai, L.-X. J. Am. Chem. Soc. 2002, 124, 2432.
40. (c) Liao, W.-W.; Li, K.; Tang, Y. J. Am. Chem. Soc. 2003, 125, 13030.
41. (d) Huang, Z.-Z.; Ye, S.; Xia, W.; Yu, Y.-H.; Tang, Y. J. Org. Chem. 2002, 67, 3096.
42. (e) Huang, Z.-Z.; Tang, Y. J. Org. Chem. 2002, 67, 5320.
43. (a) Li, K.; Huang, Z.-Z.; Tang, Y. Tetrahedron Lett. 2003, 44, 2605.
44. (b) Li, K.; Deng, X.-M.; Tang, Y. Chem. Commun. 2003, 2074.
45. For reviews on transformation of vinylsilane, see: (a) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57.
46. (b) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlage: Berlin, 1983.
47. (c) Colvin, E. W. Silicon in Organic Synthesis; Butterworths: London, 1983.
48. Dana, G.; Thuan, S. L. T.; Gharbi-Benarous, J. Bull. Soc. Chim. Fr. 1974, 2089.